Imidazole → N-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-yl)-2,2,2-trifluoroacetamide

Participants

Reaction Steps

To a 250 ml round bottom flask containing 2.2 g (8.49 mmol) of 2,2,2-trifluoro-N-((1R,4R)-4-hydroxy-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide and 1.73 g (25.48 mmol) of imidazole was added 35 ml of DMF, and stirring was started. To this solution was added 4.67 g (16.99 mmol) of t-butylchlorodiphenylsilane. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with 150 ml EtOAc, and washed with 20 ml distilled water. The organic phase was dried over MgSO4 and concentrated in vacuo and purified by column chromatography (eluting with 1:1 DCM:Hex), to give 4.0 g (95%) of the titled compound.

Provenance & Evidence